The Hardest Question Every CEO Must Answer: Would You Hire Every VP on Your Team Again?
I was having coffee with a great CEO the other day at around $30m ARR and things were getting … harder. So I asked a simple question to help identify the root causes:
“If you were hiring your VP team from scratch today, knowing what you know now, would you hire every single one of them again?” Because, usually, that’s the root cause of growth slowing. Not competition per se, AI, market changes, etc. Great teams react and in the end, get ahead of change.
Her answer? Three out of five. She’d hire 3 out of 5 of her exec team again.
I gave her an A-. That’s above average in my experience. At even the best start-ups, you are lucky if 60% of your management team is truly great.
You have to be honest and confront the same question about your own leadership team. If you can’t answer “yes” to that question about every VP on your team, you already know what you need to do.
The Hidden Tax of Wrong-Fit VPs
A VP-level hire gone wrong doesn’t just cost you their salary. Here’s what it actually costs:
- 6-12 months of lost momentum while they ramp (or fail to ramp)
- 20-40% team productivity drag as their direct reports lose confidence
- $500K-$2M in opportunity cost depending on their function
- Cascading hiring mistakes as they build out their team with the wrong people
- Cultural erosion that spreads like wildfire through the organization
But the biggest cost? Your time. As CEO, you end up doing their job while they figure it out. And — usually they don’t.
So If Growth Has Slowed Especially, This is My #1 Question: Would You Hire Your VPs Over Again?
If not, pick one to start and get going. Now. You can’t do it alone.
The Three Types of VP Misfits
In my experience, VP-level and C-level misfits fall into three buckets:
- #1. The Scale Victim They were great when you were 20 people. At 150+ people, they’re drowning. They got promoted past their capability ceiling, and now everyone can see it. These are often your earliest employees who you feel loyalty toward, making the decision even harder.
- #2. The Culture Clash Strong resume. Mostly the right experience. But they just don’t fit your culture. They’re the VP who questions every decision in public, undermines other leaders, or treats junior employees poorly. Skills aren’t the issue – judgment and values are. Move on after a few weeks. Blame yourself, not them. But move on.
- #3. The Plateau Player They’re not bad. They’re not great. They’re just… fine. They hit their numbers, manage their team adequately, and never cause drama. But they also never drive breakthrough results or inspire their organization. In a growth company, “fine” is actually terrible.
The Kindness Trap
Here’s where most CEOs get stuck: “But they’re such a good person.”
We all get it. We’ve all been there. The VP who worked 80-hour weeks in the early days. The one who took a pay cut to join your mission. The one whose family you know, whose kids you know.
But here’s the hard truth about kindness: Keeping the wrong person in a VP role isn’t kind to anyone.
It’s not kind to them – they’re set up to fail and probably know it. It’s not kind to their team – they deserve better leadership. It’s not kind to your customers – they’re getting subpar execution. It’s not kind to your investors – you’re wasting their capital. It’s not kind to your other VPs – they’re carrying extra weight.
Real kindness is helping someone find the right role where they can thrive, even if it’s not at your company.
The “Get Going” Framework
If you’ve identified VPs who don’t pass the “hire again” test, here’s how to handle it:
Step 1: Get Clear on the Gap (Week 1) Document specifically what success looks like in their role versus current performance. Be ruthlessly objective. If you can’t articulate the gap clearly, the problem might be your expectations, not their performance.
Step 2: The Direct Conversation (Week 2) Have the hard conversation. “Here’s where I need to see improvement, here’s the timeline, here are the resources I’ll provide.” No sugarcoating. No corporate speak. Just clarity.
Step 3: The 30-Day Plan — Maybe 60, But You Won’t Really Need It (Weeks 3-10) Give them a real shot with clear milestones, additional resources, coaching, whatever they need. But stick to the timeline. VPs don’t need 6 months to show improvement – 30-60 days is plenty. And the best ones know it.
Step 4: The Decision (Week 11) If they haven’t demonstrably improved, make the change. Offer a generous transition, help them find their next role, celebrate their contributions. But don’t extend the timeline.
The Succession Planning Imperative
You should already know who would replace each VP before you need to replace them. If you don’t have an internal successor identified and an external search strategy ready, you’re not ready to make necessary changes.
Start building that bench now:
- Identify high-potential directors who could step up
- Maintain relationships with great candidates in your network
- Keep your executive recruiter relationships warm
- Document what great looks like for each VP role
When You Know, You Know
I’ll leave you with this: every CEO I know who has made a difficult VP change has told me the same thing afterward: “I should have done it six months sooner.”
Your gut is usually right about people. If you’re questioning whether someone should be on your leadership team, that’s already your answer.
Be kind. Be generous. Help them transition well.
But get going.
The cost of waiting is too high – for everyone involved.
What about you? Can you honestly say you’d hire every VP on your team again? If not, what are you waiting for?
P.S. If you’re struggling with this decision, remember: the best VPs want to work with other A-players. Keeping B-players in VP roles makes it harder to attract and retain the A-players you need to scale.
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